Substituted aryl sulphonyl(thio)ureas used as herbicides

ABSTRACT

The invention relates to novel substituted arylsulphonyl(thio)ureas 
                 
 
in which
         A represents nitrogen or a CH grouping,   Q represents oxygen or sulphur,   R 1  represents hydrogen, halogen or respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy or heterocyclyloxy,   R 2  represents hydrogen, halogen or respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy or heterocyclyloxy,   R 3  represents hydrogen or optionally substituted alkyl,   R 4  represents respectively optionally substituted alkyl, alkoxy, alkenyl, alkinyl, alkenyloxy, alkinyloxy, cycloalkyl, cycloalkyloxy or cycloalkylalkyl, and   R 5  represents hydrogen, formyl or respectively optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, alkenyl, alkinyl, cycloalkyl, cycloalkylcarbonyl, cycloalkylsulphonyl or heterocyclyl,   and to salts of compounds of the formula (I),   except for the compound N-(4,6-dimethyl-pyrimidin-2-yl)-N′-[2-(1,1,2,2-tetrafluoro-ethoxy)-6-methyl-phenylsulphonyl]-urea,   to processes for preparing the novel compounds and to their use as herbicides.

This application is a divisional of application Ser. No. 09/125,997, filed on Aug. 28, 1998, now U.S. Pat. No. 6,451,737, which is a 371 application of PCT/EP97/00798, filed on Feb. 20, 1997.

The present invention relates to novel substituted arylsulphonyl(thio)ureas, to processes for their preparation and to their use as herbicides.

It is already known that certain substituted sulphonylureas have herbicidal properties (cf. DE 2715786, EP 1514, EP 23422). However, the herbicidal activity and the crop plant safety of these compounds is not satisfactory in all aspects.

This invention, accordingly, provides the novel substituted arylsulphonyl(thio)ureas of the general formula (I)

in which

-   -   A represents nitrogen or a CH grouping,     -   Q represents oxygen or sulphur,     -   R¹ represents hydrogen, halogen or respectively optionally         substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino,         cycloalkyl, cycloalkyloxy or heterocyclyloxy,     -   R² represents hydrogen, halogen or respectively optionally         substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino,         cycloalkyl, cycloalkyloxy or heterocyclyloxy,     -   R³ represents hydrogen or optionally substituted alkyl,     -   R⁴ represents respectively optionally substituted alkyl, alkoxy,         alkenyl, alkinyl, alkenyloxy, alkinyloxy, cycloalkyl,         cycloalkyloxy or cycloalkylalkyl, and     -   R⁵ represents hydrogen, formyl or respectively optionally         substituted alkyl, alkylcarbonyl, alkoxycarbonyl,         alkylsulphonyl, alkenyl, alkinyl, cycloalkyl,         cycloalkylcarbonyl, cycloalkylsulphonyl or heterocyclyl,     -   and salts of compounds of the formula (I),     -   except for the prior-art compound         N-(4,6-dimethyl-pyrimidin-2-yl)-N′-[2-(1,1,2,2-tetra-fluoro-ethoxy)-6-methyl-phenylsulphonyl]-urea         (cf. EP 23422) which is excluded by disclaimer.

The novel substituted arylsulphonyl(thio)ureas of the general formula (I) are obtained when (a) aminoazines of the general formula (II)

in which

-   -   A, R¹ and R² are each as defined above,     -   are reacted with arylsulphonyl iso(thio)cyanates of the general         formula (III)         in which     -   Q, R⁴ and R⁵ are each as defined above,     -   if appropriate in the presence of a reaction auxiliary and if         appropriate in the presence of a diluent,     -   or     -   (b) substituted aminoazines of the general formula (IV)         in which     -   A, Q, R¹ and R² are each as defined above,     -   Z represents halogen, alkoxy or aryloxy and     -   R³ is as defined above or represents the grouping —C(Q)—Z     -   are reacted with arenesulphonamides of the general formula (V)         in which     -   R⁴ and R⁵ are each as defined above,     -   if appropriate in the presence of a reaction auxiliary and if         appropriate in the presence of a diluent,     -   or     -   (c) aminoazines of the general formula (II)         in which     -   A, R¹ and R² are each as defined above,     -   are reacted with substituted arenesulphonamides of the general         formula (VI)         in which     -   Q, R⁴ and R⁵ are each as defined above and     -   Z represents halogen, alkoxy or aryloxy,     -   if appropriate in the presence of a reaction auxiliary and if         appropriate in the presence of a diluent,     -   and the compounds of the formula (I) obtained by processes         (a), (b) and (c) are, if appropriate, converted into salts by         customary methods.

The novel substituted arylsulphonyl(thio)ureas of the general formula (I) have strong herbicidal activity.

The invention preferably provides compounds of the formula (I) in which

-   -   A represents nitrogen or a CH grouping,     -   Q represents oxygen or sulphur,     -   R¹ represents hydrogen, halogen, represents respectively         optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl,         alkoxy, alkylthio, alkylamino or di-alkylamino having in each         case 1 to 4 carbon atoms in the alkyl groups, represents         respectively optionally cyano-, halogen-, C₁-C₄-alkyl- or         C₁-C₄-alkoxy-substituted cycloalkyl or cycloalkyloxy having in         each case 3 to 6 carbon atoms, or represents respectively         optionally cyano-, halogen-, C₁-C₄-alkyl- or         C₁-C₄-alkoxy-substituted oxetanyloxy, furyloxy or         tetrahydrofuryloxy.     -   R² represents hydrogen or halogen, represents respectively         optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl,         alkoxy, alkylthio, alkylamino or di-alkylamino having in each         case 1 to 4 carbon atoms in the alkyl groups, represents         respectively optionally cyano-, halogen-, C₁-C₄-alkyl- or         C₁-C₄-alkoxy-substituted cycloalkyl or cycloalkyloxy having in         each case 3 to 6 carbon atoms, or represents respectively         optionally cyano-, halogen-, C₁-C₄-alkyl- or         C₁-C₄-alkoxy-substituted oxetanyloxy, furyloxy or         tetrahydrofuryloxy,     -   R³ represents hydrogen or optionally C₁-C₄-alkoxy,         C₁-C₄-alkyl-carbonyl- or C₁-C₄-alkoxy-carbonyl-substituted alkyl         having 1 to 4 carbon atoms,     -   R⁴ represents respectively optionally cyano-, halogen- or         C₁-C₄-alkoxy-substituted alkyl or alkoxy having in each case 1         to 6 carbon atoms in the alkyl groups, represents respectively         optionally halogen-substituted alkenyl, alkinyl, alkenyloxy or         alkinyloxy having in each case 2 to 6 carbon atoms in the         alkenyl or alkinyl groups, or represents respectively optionally         cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl,         cycloalkyloxy or cycloalkylalkyl having in each case 3 to 6         carbon atoms in the cycloalkyl groups and optionally 1 to 4         carbon atoms in the alkyl moiety,     -   R⁵ represents hydrogen, formyl, represents respectively         optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl,         alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl having in each         case 1 to 6 carbon atoms in the alkyl groups, represents         respectively optionally halogen-substituted alkenyl or alkinyl         having in each case 2 to 6 carbon atoms, represents respectively         optionally cyano-, halogen- or C₁-C₄-alkyl-substituted         cycloalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl having in         each case 3 to 6 carbon atoms in the cycloalkyl groups, or         represents respectively optionally cyano-, halogen-,         C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted oxetanyl, furyl or         tetrahydrofuryl,     -   except for the prior-art compound         N-(4,6-dimethyl-pyrimidin-2-yl)-N′-[2-(1,1,2,2-tetrafluoro-ethoxy)-6-methyl-phenylsulphonyl]-urea         (cf. EP 23422) which is excluded by disclaimer.

The invention furthermore preferably provides sodium, potassium, magnesium, calcium, ammonium, C₁-C₄-alkyl-ammonium, di-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-ammonium, tetra-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-sulphonium, C₅- or C₆-cycloalkyl-ammonium and di-(C₁-C₂-alkyl)-benzyl-ammonium salts of compounds of the formula (I) in which A, Q, R¹, R², R³, R⁴ and R⁵ are each preferably as defined above.

The invention provides in particular compounds of the formula (I) in which

-   -   A represents nitrogen or a CH grouping,     -   Q represents oxygen or sulphur,     -   R¹ represents hydrogen, fluorine, chlorine, bromine or         respectively optionally cyano-, fluorine-, chlorine-, methoxy-         or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy,         ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or         i-propylthio, methylamino, ethylamino, n- or i-propylamino,         dimethylamino or diethylamino,     -   R² represents fluorine, chlorine, bromine or respectively         optionally cyano-, fluorine-, chlorine-, methoxy- or         ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy,         ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or         i-propylthio, methylamino, ethylamino, n- or i-propylamino,         dimethylamino or diethylamino,     -   R³ represents hydrogen or optionally methoxy-, ethoxy-, n- or         i-propoxy-, acetyl-, propionyl-, n- or i-butyroyl-,         methoxycarbonyl-, ethoxycarbonyl-, n- or         i-propoxycarbonyl-substituted methyl or ethyl,     -   R⁴ represents respectively optionally cyano-, fluorine-,         chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or         i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or         i-propoxy, n-, i-, s- or t-butoxy, represents respectively         optionally fluorine-, chlorine- or bromine-substituted propenyl,         butenyl, propinyl, butinyl, propenyloxy, butenyloxy, propinyloxy         or butinyloxy, or represents respectively optionally cyano-,         fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or         i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,         cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,         cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl,         cyclopentylmethyl or cyclohexylmethyl,     -   R⁵ represents hydrogen, formyl, represents respectively         optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n-         or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-,         s- or t-butyl, acetyl, propionyl, n- or i-butyroyl,         methoxycarbonyl ethoxycarbonyl, n- or i-propoxycarbonyl,         methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl,         represents respectively optionally fluorine-, chlorine- or         bromine-substituted propenyl, butenyl, propinyl or butinyl, or         represents respectively optionally cyano-, fluorine-, chlorine-,         bromine-, methyl-, ethyl-, n- or i-propyl-substituted         cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,         cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl,         cyclohexylcarbonyl, cyclopropylsulphonyl, cyclobutylsulphonyl,         cyclopentylsulphonyl or cyclohexylsulphonyl,     -   except for the prior-art compound         N-(4,6-dimethyl-pyrimidin-2-yl)-N′-[2-(1,1,2,2-tetrafluoro-ethoxy)-6-methyl-phenylsulphonyl]-urea         (cf. EP 23422) which is excluded by disclaimer.

The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, that is to say combinations between the ranges of preferred compounds indicated are also possible.

Examples of the compounds of the formula (I) according to the invention are listed in the groups below.

Group 1

(Ia-1)

A, Q, R¹, R² and R³ have, for example, the meaning listed below: A Q R¹ R² R³ CH O OCH₃ OCH₃ H CH O CH₃ OCH₃ H CH O CH₃ CH₃ H CH O Cl OCH₃ H CH O H CH₃ H N O CH₃ OCH₃ CH₃ N O OCH₃ OCH₃ CH₃ N O CH₃ OCH₃ H N O OCH₃ OCH₃ H N O CH₃ CH₃ H N O OCHF₂ N(CH₃)₂ H N O CH₃ SCH₃ H N O C₂H₅ OCH₃ H N O CH₃ OC₂H₅ H N O H OCH₃ H N O OCH₃

H N O CH₃ N(CH₃)₂ H CH O OCH₃

H CH O

H CH O CH₃

H CH O Cl

H N O

H N O CH₃

H N O H

H N S CH₃ OCH₃ H Group 2

A, Q, R¹, R² and R³ have, for example, the meaning given above in group 1. Group 3

A, Q, R¹, R² and R³ have, for example, the meaning given above in group 1. Group 4

A, Q, R¹, R² and R³ have, for example, the meaning given above in group 1. Group 5

A, Q, R¹, R² and R³ have, for example, the meaning given above in group 1. Group 6

A, Q, R¹, R² and R³ have, for example, the meaning given above in group 1. Group 7

A, Q, R¹, R² and R³ have, for example, the meaning given above in group 1. Group 8

A, Q, R¹, R² and R³ have for example, the meaning given above in group 1. Group 9

A, Q, R¹, R² and R³ have for example, the meaning given above in group 1. Group 10

A, Q, R¹, R² and R³ have for example, the meaning given above in group 1. Group 11

A, Q, R¹, R² and R³ have, for example, the meaning given above in group 1. Group 12

A, Q, R¹, R² and R³ have, for example, the meaning given above in group 1. Group 13

A, Q, R¹, R² and R³ have, for example, the meaning given above in group 1. Group 14

A, Q, R¹, R² and R³ have, for example, the meaning given above in group 1.

Using, for example, 2-amino-4-methoxy-6-methyl-pyrimidine and 2-ethoxy-6-trifluoromethyl-phenylsulphonyl isocyanate as starting materials, the course of the reaction in the process (a) according to the invention can be illustrated by the following equation:

Using, for example, 2-methoxycarbonylamino-4-methoxy-6-trifluoromethyl-1,3,5-triazine and 2-methyl-6-trifluoromethoxy-benzenesulphonamide as starting materials, the course of the reaction in the process (b) according to the invention can be illustrated by the following equation:

Using, for example, 2-amino-4-chloro-6-methoxy-pyrimidine and N-(2,6-dimethoxy-phenylsulphonyl)-O-phenyl-urethane as starting materials, the course of the reaction in the process (c) according to the invention can be illustrated by the following equation:

The formula (II) provides a general definition of the aminoazines to be used as starting materials in the processes (a) and (c) for preparing compounds of the general formula (I). In the formula (II), A, R¹ and R² each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or particularly preferred for A, R¹ and R².

The aminoazines of the formula (II) are known chemicals for synthesis, some of which are commercially available.

The formula (III) provides a general definition of the arylsulphonyl iso(thio)cyanates further to be used as starting materials in the process (a) according to the invention. In the formula (III), Q, R⁴ and R⁵ each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or particularly preferred for Q, R⁴ and R⁵.

The starting materials of the formula (III) are known and/or can be prepared by processes known per se (cf. DE 3208189, EP 23422, EP 64322, EP 44807, EP 216504, Preparation Examples).

The arylsulphonyl iso(thio)cyanates of the formula (III) are obtained when arenesulphonamides of the general formula (V)—above—are reacted with phosgene or thiophosgene, if appropriate in the presence of an alkyl isocyanate, such as, for example, butyl isocyanate, if appropriate in the presence of a reaction auxiliary, such as, for example, diazabicyclo[2.2.2]-octane, and in the presence of a diluent, such as, for example, toluene, xylene or chlorobenzene, at temperatures between 80° C. and 150° C., and the volatile components are distilled off under reduced pressure after the reaction has ended.

The formula (IV) provides a general definition of the substituted aminoazines to be used as starting materials in the process (b) according to the invention for preparing compounds of the formula (I). In the formula (IV), A, Q, R¹ and R² each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or particularly preferred for A, Q, R¹ and R²; Z preferably represents fluorine, chlorine, bromine, C₁-C₄-alkoxy or phenoxy, in particular chlorine, methoxy, ethoxy or phenoxy.

The starting materials of the formula (IV) are known and/or can be prepared by processes known per se (cf. U.S. Pat. No. 4,690,707, DE 19501174, Preparation Examples).

The formula (V) provides a general definition of the arenesulphonamides further to be used as starting materials in the process (b) according to the invention. In the formula (V), R⁴ and R⁵ each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or particularly preferred for R⁴, and R⁵.

The starting materials of the formula (V) are known and/or can be prepared by a process known per se (cf. DE 3208189, EP 23422, EP 64322, EP 44807, EP 216504, DE 19525162, Preparation Examples).

The formula (VI) provides a general definition of the substituted arenesulphonamides to be used as starting materials in the process (c) according to the invention for preparing the compounds of the formula (I). In the formula (VI), Q, R⁴ and R⁵ each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or particularly preferred for Q, R⁴ and R⁵; Z preferably represents fluorine, chlorine, bromine, C₁-C₄-alkoxy or phenoxy, in particular chlorine, methoxy, ethoxy or phenoxy.

The starting materials of the formula (VI) are known and/or can be prepared by processes known per se (cf. the Preparation Examples).

Suitable diluents for carrying out the processes (a), (b) and (c) according to the invention are inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitrites, such as acetonitrile, propionitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate; sulphoxides, such as dimethyl sulphoxide; alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, mixtures thereof with water or pure water.

The processes (a), (b) and (c) according to the invention are preferably carried out in the presence of a suitable reaction auxiliary. Suitable reaction auxiliaries are all customary inorganic or organic bases. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as, for example, sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

When carrying out the processes (a), (b) and (c) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the reaction is carried out at temperatures between −20° C. and +150° C., preferably between 0° C. and +120° C.

The processes (a), (b) and (c) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure—generally between 0.1 bar and 10 bar.

In the practice of the processes (a), (b) and (c) according to the invention, the starting materials are generally employed in approximately equimolar amounts. However, it is also possible to employ one of the components in a relatively large excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred for a number of hours at the temperature required. Work-up is carried out by customary methods (cf. the Preparation Examples).

If required, salts can be prepared from the compounds of the general formula (I) according to the invention. Such salts are obtained in a simple manner by customary methods of forming salts, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent, such as, for example, methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable base. The salts can then be isolated—if required after prolonged stirring—by concentration or filtration with suction.

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed killers. By weeds in the broadest sense, there are to be understood all plants which grow in locations where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in connection with the following plants:

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledonous crop plants of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledonous crop plants of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.

The compounds are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and railway tracks, and on paths and squares with or without tree plantings. Likewise, the compounds can be employed for controlling weeds in perennial cultures, for example forests, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop fields, on lawns, sports fields and pasture-land, and for the selective control of weeds in annual cultures.

The compounds of the formula (I) according to the invention are suitable in particular for controlling monocotyledonous and dicotyledenous weeds, both pre-emergence and post-emergence. They have strong herbicidal activity and a broad spectrum of activity when applied to the soil and to the above-ground parts of plants.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersing agents and/or foam-forming agents.

If the extender used is water, it is also possible to employ for example organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and water.

Suitable solid carriers are:

-   -   for example ammonium salts and ground natural minerals, such as         kaolins, clays, talc, chalk, quartz, attapulgite,         montmorillonite or diatomaceous earth, and ground synthetic         minerals, such as finely divided silica, alumina and silicates,         suitable solid carriers for granules are: for example crushed         and fractionated natural rocks such as calcite, marble, pumice,         sepiolite and dolomite, as well as synthetic granules of         inorganic and organic meals, and granules of organic material         such as sawdust, coconut shells, maize cobs and tobacco stalks;         suitable emulsifiers and/or foam-forming agents are: for example         nonionic and anionic emulsifiers, such as polyoxyethylene fatty         acid esters, polyoxyethylene fatty alcohol ethers, for example         alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates,         arylsulphonates as well as protein hydrolysates; suitable         dispersing agents are: for example lignin-sulphite waste liquors         and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention, such as or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.

Possible components for the mixtures are known herbicides, for example anilides such as, for example, diflufenican and propanil; arylcarboxylic acids such as, for example, dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids such as, for example, 2,4 D, 2,4 DB, 2,4 DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones such as, for example, chloridazon and norflurazon; carbamates such as, for example, chlorpropham, desmedipham, phenmedipham and propham; chloroacetanilides such as, for example, alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; dinitroanilines such as, for example, oryzalin, pendimethalin and trifluralin; diphenyl ethers such as, for example, acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas such as, for example, chlortoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylamines such as, for example, alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones such as, for example, imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles such as, for example, bromoxynil, dichlobenil and ioxynil; oxyacetamides such as, for example, mefenacet; sulphonylureas such as, for example, amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiocarbamates such as, for example, butylate, cycloate, di-allate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and tri-allate; triazines such as, for example, atrazine, cyanazine, simazine, simetryn, terbutryn and terbutylazine; triazinones such as, for example, hexazinone, metamitron and metribuzin; others such as, for example, aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.

Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the examples below.

PREPARATION EXAMPLES Example 1

(Process (b))

At about 20° C., a mixture of 1.43 g (5.6 mmol) of 2-methoxy-6-trifluoromethyl-benzenesulphonamide, 1.24 g (5.1 mmol) of 2-phenoxycarbonylamino-4,6-dimethyl-pyrimidine, 0.85 g (5.6 mmol) of diazabicycloundecene (DBU) and 50 ml of acetonitrile is stirred for 15 hours. The mixture is then concentrated using water pump vacuum and the residue is stirred with 50 ml of 1N hydrochloric acid and 50 ml of methylene chloride. The organic phase is separated off, washed with water, dried with sodium sulphate and filtered. The filtrate is concentrated using water pump vacuum, the residue is digested with i-propanol and the crystalline product is isolated by filtration with suction.

This gives 1.6 g (62% of theory) of N-(4,6-dimethyl-pyrimidin-2-yl)-N′-(2-methoxy-6-trifluoromethyl-phenylsulphonyl)-urea of melting point 190° C.

Example 2

(Process (b))

At about 20° C., a mixture of 2.0 g (10 mmol) of 2-methoxy-6-methyl-benzenesulphonamide, 4.0 g (10 mmol) of N,N-bis-phenoxycarbonyl-2-amino-4,6-dimethoxy-1,3,5-triazine, 1.1 g (10 mmol) of potassium t-butoxide and 50 ml of acetonitrile is stirred for 15 hours. The mixture is then concentrated using water pump vacuum and the residue is stirred with 50 ml of 1N hydrochloric acid and 50 ml of methylene chloride. The organic phase is separated off, washed with water, dried with sodium sulphate and filtered. The filtrate is concentrated using water pump vacuum, the residue is digested with i-propanol and the resulting crystalline product is isolated by filtration with suction.

This gives 2.1 g (55% of theory) of N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N′-(2-methoxy-6-methyl-phenylsulphonyl)-urea of melting point 163° C.

Example 3

(Process (c) with precursor)

At about 20° C., 1.6 g (10 mmol) of phenyl chloroformate are added dropwise to a mixture of 2.2 g (10 mmol) of 2-ethoxy-6-methyl-benzenesulphonamide, 2.0 g (20 mmol) of triethylamine and 30 ml of acetonitrile, and the mixture is stirred at the temperature stated for about 30 minutes. 1.0 g (10 mmol) of methanesulphonic acid and 1.6 g (10 mmol) of 2-amino-4,6-dimethoxy-pyrimidine are then added, and the reaction mixture is stirred at about 60° C. for about 15 minutes. The mixture is cooled to about 20° C. and filtered with suction, the filtrate is concentrated using water pump vacuum and the residue is stirred with 30 ml of 1N hydrochloric acid. Filtration with suction and drying gives a crude product which is purified by rinsing with diethyl ether.

Yield: 2.2 g (55%) of theory) of N-(4,6-dimethoxy-pyrimidin-2-yl)-N′-(2-ethoxy-6-methyl-phenylsulphonyl)-urea of melting point 184° C.

Similar to Preparation Examples 1 to 3, and in accordance with the general description of the preparation processes according to the invention, it is also possible to prepare, for example, the compounds of the formula (I) listed in Table 1 below.,

TABLE 1 Examples of compounds of the formula (I) (I)

Ex. Melting No. A Q R¹ R² R³ R⁴ R⁵ point (° C.)  4 N O CH₃ OCH₃ H CF₃ C₂H₅ 115  5 N O CH₃ OCH₃ H CF₃ CH₃ 214  6 N O OCH₃ OCH₃ H CF₃ CH₃ 189  7 N O OCH₃ OCH₃ H CF₃ C₂H₅ 176  8 CH O CH₃ CH₃ H CF₃ C₂H₅ 214  9 N O CH₃ OCH₃ H CF₃ C₃H₇-n 142 10 N O OCH₃ OCH₃ H CF₃ C₃H₇-n 162 11 CH O CH₃ CH₃ H CF₃ C₃H₇-n 212 12 N O CH₃ OCH₃ H CF₃ C₃H₇-i 168 13 N O OCH₃ OCH₃ H CF₃ C₃H₇-i 200 14 CH O CH₃ CH₃ H CF₃ C₃H₇-i 221 15 CH O Cl OCH₃ H CF₃ CH₃ 224 16 CH O Cl OCH₃ H CF₃ C₂H₅ 176 17 CH O Cl OCH₃ H CF₃ C₃H₇-n 169 18 N O N(CH₃)₂ OCH₂CF₃ H CF₃ CH₃ 222 19 N O N(CH₃)₂ OCH₂CF₃ H CF₃ C₂H₅ 209 20 N O N(CH₃)₂ OCH₂CF₃ H CF₃ C₃H₇-n 175 21 N O N(CH₃)₂ OCH₂CF₃ H CF₃ C₃H₇-i 204 22 CH O OCH₃ OCH₃ H CF₃ CH₃ 111 (decomp.) 23 CH O OCH₃ OCH₃ H CF₃ C₂H₅  99 (decomp.) 24 CH O OCH₃ OCH₃ H CF₃ C₃H₇-n 180 25 CH O OCH₃ OCH₃ H CF₃ C₃H₇-i  98 (decomp.) 26 CH O CH₃ CH₃ H CH₃ C₂H₅ 217 27 CH O CH₃ OCH₃ H CH₃ C₂H₅ 183 28 CH O H CH₃ H CH₃ C₂H₅ 190 29 CH O CH₃ CH₃ H CH₃ C₃H₇-n 194 30 CH O H CH₃ H CH₃ C₃H₇-n 176 31 N O OCH₃ OCH₃ H CH₃ C₂H₅ 181 32 N O CH₃ OCH₃ H CH₃ C₂H₅ 170 33 CH O CH₃ OCH₃ H CH₃ C₃H₇-i 196   34¹⁾ CH O OCH₃ OCH₃ H CH₃

204 35 CH O CH₃ CH₃ H CH₃ C₃H₇-i 231 36 CH O OCH₃ OCH₃ H CH₃ C₃H₇-i 190 37 CH O H CH₃ H CH₃ C₃H₇-i 206 38 N O OCH₃ OCH₃ H CH₃ C₃H₇-i 191 39 N O OCH₃ OCH₃ H CH₃ C₃H₇-i 205 40 N O CH₃ OCH₃ H CH₃ CH₃ 193 41 CH O CH₃ CH₃ H CH₃ CH₃ 220 42 CH O H CH₃ H CH₃ CH₃ 206 43 CH O CH₃ OCH₃ H CH₃ CH₃ 172 44 CH O OCH₃ OCH₃ H CH₃ CH₃ 142 45 N O N(CH₃)₂ OCH₂CF₃ H CH₃ C₂H₅ 187 46 CH O CH₃ OCH₃ H CH₃ C₃H₇-n 147 47 CH O OCH₃ OCH₃ H CH₃ C₃H₇-n 164 48 N O OCH₃ OCH₃ H CH₃ C₃H₇-n 156 49 N O CH₃ OCH₃ H CH₃ C₃H₇-n 150 50 CH O OCH₃ OCH₃ H C₃H₇-i C₂H₅ 184 51 N O OCH₃ OCH₃ H C₃H₇-i C₂H₅ 157 52 N O N(CH₃)₂ OCH₂CF₃ H CH₃ CH₃ 214 53 N O N(CH₃)₂ OCH₂CF₃ H CH₃ C₃H₇-i 202 54 CH O OCH₃ OCH₃ H CH₃

171 55 N O OCH₃ OCH₃ H CH₃

198 56 N O CH₃ OCH₃ H CH₃

183 57 N O OCH₃ OCH₃ H CH₃ C₄H₉-s 174 58 CH O CH₃ OCH₃ H CH₃ C₄H₉-s 186 59 N O CH₃ OCH₃ H CH₃ C₄H₉-s 177 60 CH O CH₃ CH₃ H CH₃ C₄H₉-s 228 61 CH O OCH₃ OCH₃ H CH₃ C₄H₉-s 207 62 CH O CH₃ CF₃ H CH₃ C₃H₇-i 192 63 CH O CH₃ CF₃ H CH₃ CH₃ 209 64 N O CH₃ OCH₃ H C₃H₇-i CH₃ 136 65 CH O OCH₃ OCH₃ H CH₃ CHF₂ 170 66 N O CH₃ OCH₃ H CH₃ CHF₂ 197 67 N O OCH₃ OCH₃ H OC₃H₇-n C₃H₇-n 140 68 CH O Cl OCH₃ H OCH₃ C₃H₇-i 148 69 N O CH₃ OCH₃ H OCH₃ C₃H₇-i 152 70 N O CH₃ OCH₃ H OC₄H₉-n C₄H₉-n  90 71 N O CH₃ OCH₃ H OC₃H₇-i C₃H₇-i  80 72 N O CH₃ OCH₃ H OC₂H₅ C₃H₇-i 118 73 N O CH₃ OCH₃ Na OCH₃ CH₃ 203 74 CH O OCH₃ OCH₃ H C₃H₇-i CH₃ 164 75 CH O OCH₃ OCH₃ H C₃H₇-i C₃H₇-n 157 76 CH O CH₃ CF₃ H CH₃ C₂H₅ 179 77 N O CH₃ CH₃ H CF₃ CH₃ 155 78 N O CH₃ SCH₃ H CF₃ CH₃ 178 79 N O CH₃ N(CH₃)₂ H CF₃ CH₃ 213 80 N O CH₃ OC₂H₅ H CF₃ CH₃ 121 81 N O C₂H₅ OCH₃ H CF₃ CH₃ 117 82 N O OCH₂CF₂CHF₂ N(CH₃)₂ H CF₃ CH₃ 185 83 N O CH₃ OCH₃ Na C₃H₇-i CH₃ 170 84 N O OCH₃ OCH₃ H C₃H₇-i C₃H₇-n 149 85 N O OCH₃ OCH₃ H C₃H₇-i CH₃ 187 86 N O CH₃ OCH₃ H C₃H₇-i C₂H₅ 163 87 CH O CH₃ OCH₃ H C₃H₇-i CH₃ 175 88 CH O CH₃ OCH₃ H C₃H₇-i C₃H₇-i 152 89 CH O OCH₃ OCH₃ H C₃H₇-i C₃H₇-i 138 90 N O CH₃ OCH₃ Na CH₃ CH₃ 149 91 N O CH₃ CH₃ H

125 92 N O CH₃ OCH₃ Na OC₃H₇-i C₃H₇-i 178 93 N O Cl OCH₃ Na OCH₃ C₃H₇-i 172 94 N O CH₃ OCH₃ Na OC₂H₅ C₂H₅ 145   95²⁾ N O CH₃ OCH₃ Na OCH₃ C₃H₇-n NMR data 96 N O OCH₃ OCH₃ H OCH₃ C₂H₅ 110 97 N O OCH₃ OCH₃ H OC₂H₅ C₂H₅ 142 98 N O OCH₃ OCH₃ H OCH₃ C₃H₇-n 188 99 N O OCH₃ OCH₃ H OC₂H₅ C₄H₉-s 136 100  CH O Cl OCH₃ H OCH₃ C₂H₅ 146 101  CH O Cl OCH₃ H OCH₃ C₃H₇-n 110 102  CH O Cl OCH₃ H OCH₃ C₄H₉-n 117 103  CH O Cl OCH₃ H OC₄H₉-n C₄H₉-n 135 104  CH O Cl OCH₃ H OC₂H₅ C₄H₉-n 128 105  N O CH₃ OCH₃ H OC₂H₅ C₃H₇-n 110 106  N O CH₃ OCH₃ H OCH₃ CH₃ 177 107  N O CH₃ OCH₃ H OCH₃

166 108  N O CH₃ OCH₃ H OC₂H₅ C₄H₉-i  85 109  N O CH₃ OCH₃ H OCH₃ C₂H₅ 148 110  N O CH₃ OCH₃ H OCH₃ C₄H₉-n 125 111  N O CH₃ OCH₃ H OC₂H₅

130 112  CH O OCH₃ OCH₃ H CH₃ CF₃ 178 113  N O CH₃ OCH₃ H CH₃ CF₃ 178 114  CH O OCH₃ OCH₃ H C₂H₅ CF₃ 147 115  N O CH₃ OCH₃ H C₂H₅ CF₃ 140 116  CH O OCH₃ OCH₃ H CH₃ CF₂CHF₂ 169 117  N O CH₃ OCH₃ H CH₃ CF₂CHF₂ 184 118  CH O OCH₃ OCH₃ H CH₃ CH₂CF₃ 184 119  N O CH₃ OCH₃ H CH₃ CH₂CF₃ 178 120  CH O OCH₃ OCH₃ H C₂H₅ CHF₂ 110 121  N O CH₃ OCH₃ H C₂H₅ CHF₂ 157 122  CH O OCH₃ OCH₃ H C₃H₇-n CF₃ 147 123  N O CH₃ OCH₃ H C₃H₇-n CF₃  77 Notes: ¹⁾In Example 34,

is propargyl = CH₂—C≡CH ²⁾NMR data for Example 95: ¹H-NMR (300MHz; D₂O): δ = 0.96 (t, CH₃); 1.77 (m, O—CH₂—CH ₂—CH₃); 2.42 (s, CH₃); 3.87 (s, OCH₃); 3.98 (s, OCH₃); 4.04 (t, O—CH₂—); 6.79 (brd.d, 2 aromat. H); 7.48 (brd.t, 1 aromat. H) ppm. Starting Material of the Formula (III):

Example (III-1)

21.5 g (0.1 mol) of 2-ethoxy-6-methyl-benzenesulphonamide and 10 g (0.1 mol) of n-butyl isocyanate are heated to the boil in 100 ml of chlorobenzene. At reflux temperature, phosgene is introduced for 4 hours. The clear solution is concentrated under reduced pressure and the residue is subjected to precision distillation. At a pressure of 0.8 mbar and an overhead temperature of 135-140° C., 2-ethoxy-6-methyl-phenylsulphonyl isocyanate passes over and solidifies in the receiving flask.

This gives 7.9 g of 2-ethoxy-6-methyl-phenylsulphonyl isocyanate as a colourless product of melting point 40° C.

Starting Materials of the Formula (IV):

Example (IV-1)

70 g (0.44 mol) of phenyl chloroformate are added dropwise with stirring to a mixture of 31 g (0.20 mol) of 2-amino-4,6-dimethoxy-s-triazine and 100 ml of pyridine. The reaction mixture is stirred at 20° C. to 25° C. for about 15 hours and subsequently concentrated using water pump vacuum. The residue is taken up in water and then acidified using conc. hydrochloric acid. The resulting crystalline product is isolated by filtration with suction.

This gives 74.2 g (91% of theory) of 2-(N,N-bis-phenoxycarbonyl-amino)-4,6-dimethoxy-s-triazine of melting point 125° C.

Starting Materials of the Formula (V):

Example (V-1)

At 20° C., 64.6 g (0.26 mol) of 2-isopropoxy-6-methyl-benzenesulphonyl chloride are stirred in 350 ml of 25% strength aqueous ammonia solution for 12 hours. The resulting crystalline product is subsequently isolated by filtration with suction.

This gives 54 g (90% of theory) of 2-isopropoxy-6-methyl-benzenesulphonamide of melting point 78° C.

Use Examples Example A

Pre-emergence Test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the preparation of the active compound. Advantageously, the amount of water per unit area is kept constant. The active compound concentration in the preparation is not important, only the active compound application rate per unit area is critical.

After three weeks, the degree of damage to the plants is rated in % damage in comparison with the development of the untreated control.

The figures denote:

-   -   0%=no effect (like untreated control)     -   100%=total destruction

In this test, for example, the compounds of Preparation Example 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 22, 27, 31, 32, 33, 34, 38, 39, 40, 41, 43, 44, 46, 48, 49, 56, 65 and 66 exhibit, at application rates between 30 g and 125 g of a.i. per hectare, very strong activity against weeds.

-   -   “a.i.”=“active ingredient”

TABLE A Pre-emergence test/greenhouse Active compound Appli- of Prep- cation aration rate Example (g of Alope- Lo- Sor- Amaran- Cheno- Stel- No. ai./ha) curus lium ghum thus podium taria  4 60 100 100 100 100 100  95  5 60 100 100 100 100 100 100  6 60 100 100 100 100 100 100  7 60 100  95 100  95 100  95  1 60 100 100 100 100 100 100  8 30 100 100 100 —  80  90  9 30 100 100  90 100 100 100 10 60 100 100 100 100 100 100 11 60 100 100 100 100 100  95 12 30 100 100 100 100  95 100 13 60 100 100 100 100 100 100 14 30 100 100  95 —  95  95 15 60 100  95  95  95 100  95 16 30 100 —  80 — 100  90 22 30 100 —  95 100 100 100 27 60 100 100 100 100 100 100  3 60  95  60  80  80  95  95 31 60  95 100  90  95 100  95 32 60  95 100  95 100 100 100 33 30 100  95 100 —  70  90 34 30 100 —  90 —  90  90 38 30 100 100 100  80 100 100 39 30 100 100 100 100 100 100 40 30 100 100 100 100 100 100 41 30  95 100 100  60 100  80 43 30 100 100 100 100 100 100 44 30 100 100 100 100 100 100  2 30 100 100 100 100 100 100 46 60 100  90 100  90 100  80 48 60 100 100 100 100 100 100 49 30 100 100 100 100 100 100 56 60 100 100  90 100 100 100 65 125   95  70 —  95  95  95 66 60  95  95  95  95  95  95

Example B

Post-emergence Test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is chosen so that the amounts of active compound desired in each case are applied in 1000 l of water/ha.

After three weeks, the degree of damage to the plants is rated in % damage in comparison with the development of the untreated control.

The figures denote:

-   -   0%=no effect (like untreated control)     -   100%=total destruction

In this test, for example, the compounds of Preparation Example 2, 3, 4, 5, 6, 7, 8, 9, 12, 15, 16, 17, 22, 23, 24, 25, 27, 31, 32, 34, 38, 39, 40, 41, 43, 44, 48, 49, 51, 65 and 66 exhibit very strong activity against weeds.

TABLE B Post-emergence test/greenhouse Active compound Application of Preparation rate Alope- Echino- Abu- Matri- Example No. (g of ai./ha) curus chloa tilon caria  4 30 90 90 100 100  5 30 80 100  100 100  6 30 60 100   90 100  7 30 95 95  95 100  8 30 80 90  90 100  9  8 90 80 100  95 12 30 95 90  95 100 15 60 70 90  95 100 16 30 70 70 100 100 17 30 — 70  90  95 22 30 60 80  95  95 23 30 60 70  95  95 24 30 60 70  95  95 25 30 60 70  95  90 27 60 95 95 100  90  3 60 90 80 100  95 31 60 80 80 100 100 32 60 70 90 100 100 34 30 60 80  90  90 38 30 60 70  95  95 39 30 90 95 100 100 40 30 100  95  95 100 41 30 60 95  90  70 43 30 60 95 100 100 44 30 60 90 100 100  2 30 90 90  95 100 48 60 95 70 100  90 49 30 90 80 100 100 51 60 80 90 100  90 65 125  90 90 100 100 66 60 80 80 100 100 

1. A compound of formula (I)

in which A represents a CH grouping, Q represents oxygen or sulphur, R¹ represents hydrogen, halogen, represents respectively optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents respectively optionally cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms, or represents respectively optionally cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted oxetanyloxy, furyloxy or tetrahydrofuryloxy, R² represents respectively optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents respectively optionally cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms, or represents respectively optionally cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted oxetanyloxy, furyloxy or tetrahydrofuryloxy, R³ represents hydrogen or optionally C₁-C₄-alkoxy, C₁-C₄-alkyl-carbonyl- or C₁-C₄-alkoxy-carbonyl-substituted alkyl having 1 to 4 carbon atoms, R⁴ represents halogen-substituted C₁-C₆alkyl, R⁵ represents hydrogen, formyl, represents respectively optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, represents respectively optionally halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, represents respectively optionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups, or represents respectively optionally cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted oxetanyl, furyl or tetrahydrofuryl, or a salt of the compound of formula (I).
 2. A compound of formula (I) according to claim 1, wherein A represents a CH grouping, Q represents oxygen or sulphur, R¹ represents hydrogen, fluorine, chlorine, bromine or respectively optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, R² represents fluorine, chlorine, bromine or respectively optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, R³ represents hydrogen or optionally methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl or ethyl, R⁴ represents fluorine-, or chlorine-, substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R⁵ represents hydrogen, formyl, represents respectively optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, represents respectively optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl or butinyl, or represents respectively optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cyclopropylsulphonyl, cyclobutylsulphonyl, cyclopentylsulphonyl or cyclohexylsulphonyl, or the sodium, potassium, magnesium, calcium, ammonium, C₁-C₄alkyl-ammonium, di-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-ammonium, tetra-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-sulphonium, C₅- or C₆-cycloalkyl-ammonium and di-(C₁-C₂-alkyl)-benzyl-ammonium salt of the compound of formula (I).
 3. A compound of the formula (I)

wherein: A is a CH grouping, Q is oxygen, R¹ is selected from the group consisting of hydrogen, halogen, C₁-C₄-alkyl, C₁-C₄-dialkylamino and optionally halogen-substituted C₁-C₄-alkoxy, R² is selected from the group consisting of C₁-C₄-alkyl, C₁-C₄-alkythio, C₁-C₄-dialkylamino and optionally halogen-substituted C₁-C₄-alkoxy, R³ is hydrogen, R⁴ is halogen-substituted C₁-C₆alkyl, R⁵ is optionally halogen-substituted C₁-C₄-alkyl or represents a C₃-C₆-cycloalkyl, or the sodium, potassium, magnesium, calcium, ammonium C₁-C₄-alkyl-ammonium, di-(C₁-C₄alkyl)-ammonium, tri-(C₁-C₄-alkyl)-ammonium, tetra-(C₁-C₄)-ammonium, tri-(C₁-C₄-alkyl)-sulphonium, C₅ or C₆-cycloalkyl-ammonium and di-(C₁-C₂alkyl)-benzyl-ammonium salt of the compound of formula (I).
 4. The compound of formula (I) according to claim 3, wherein: A is a CH grouping, Q is oxygen, R¹ selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, dimethylamino, diethylamino, methoxy, ethoxy, n-propoxy and i-propoxy, wherein methoxy, ethoxy, n-propoxy and i-propoxy are optionally substituted with fluorine or chlorine, R² is selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, methylthio, ethylthio, n-propylthio, i-propylthio, dimethylamino, diethylamino, methoxy, ethoxy, n- and i-propoxy, wherein methoxy, ethoxy, n-propoxy and i-propoxy are optionally substituted with fluorine or chlorine, R³ is hydrogen, R⁴ is selected from the group consisting of: fluorine- or chlorine-substituted methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, R⁵ is (a) optionally fluorine- or chlorine-substituted methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl; or (b) cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
 5. A compound of formula (I)

wherein: A is a CH grouping, Q is oxygen, R¹ is selected from the group consisting of hydrogen, methyl, chlorine, methoxy and oxetanyl, R² is selected from the group consisting of methyl, methoxy, chlorine and oxetanyl, R³ is hydrogen, R⁴ is trifluoromethyl, R⁵ is selected from the group consisting of methyl, diffluoromethyl, trifluoromethyl, ethyl, methoxy, n-propyl, i-propyl, cyclopentanyloxy and oxetanyl, or the sodium, potassium, magnesium, calcium, ammonium, C₁-C₄-alkyl-ammonium, di-(C₁-C₄) alkyl)-ammonium, tri(C₁-C₄)-ammonium, tetra-(C₁-C₄)-ammonium, tetra-(C₁-C₄alkyl)-sulphonium, C₅- or C₆-cycloalkyl-ammonium and di-(C₁-C₂alkyl)-benzyl-ammonium salt of the compound of formula (I).
 6. A compound of formula (I), wherein:

A is a CH grouping, Q is oxygen, R¹ is selected from the group consisting of hydrogen, methyl, methoxy and chlorine, R² is selected from the group consisting of methyl and methoxy, R³ is hydrogen, R⁴ is selected from the group consisting of trifluoromethyl, R⁵ is selected from the group consisting of methyl, difluoromethyl, trifluoromethyl, ethyl, —CF₂CHF₂, —CH₂CF₃, n-propyl, i-propyl, s-butyl, propargyl and cyclopentanyl.
 7. Herbicidal compositions, which is comprised of one or more compound of the formula (I) according to claim 1 and a herbicidally acceptable carrier or diluent.
 8. The method for controlling undesirable plant growth which comprises of administering an effective amount of one or more compound of formula (I) according to claim
 1. 9. A method for controlling weeds wherein an effective amount of compound formula (I) according to claim 1 are allowed to act on the weeds or their habitat. 